14 People Share Their Most Awkward Attempts At Flirting


I don’t flirt because I suck at it.

You’re about to meet 14 people who flirted and failed miserably.

After reading many of these, I feel very good about my decision to not flirt.

14. SQUIRT!!!

I went to Israel on birthright. towards the beginning of the trip, we had a 5 hour bus ride through the desert. I was pretty sleep deprived already and somehow managed to get the best looking girl on the trip to sit with me for the ride. After an hour or so of chatting it up, I decided to take it to the next level, and put my arm around her. Surprisingly, she was into it. We both fell asleep like this for around 20 mins.

We then woke up and she went to take a drink from her 1 liter water bottle. I decide for some completely unknown reason that it would be funny and flirty to squeeze the hell out of the bottle. It explodes all over her face and clothes drenching her. I was almost as surprised as she was.

I instantly apologized for my “joke” and we rode for endless hours through the desert in moist awkward silence and I blew my chances obviously.

TL:DR- Had a long bus ride with a hot girl, squirted all over her face, she was not pleased.

13. What’s The Rub?

Oh man. This one burns to relive. About a year and a half ago, I flew into Montana and drove straight to Jackson Hole, Wyoming, with a good buddy of mine. We started drinking pretty heavily at the rodeo, and decided to eventually saddle up at the Million Dollar Cowboy bar.

When we walked in, there was space at the back bar, so we took our positions. Within minutes, we were surrounded by 20 girls from a bachelorette party. Money.

Pause for relevant context: * I had been up for about 20 hours off of 3 hours of sleep * I don’t have cash, and this is an all cash bar * My buddy, now sitting on my left, is very smooth with girls, and I was in the middle of a dry spell

One of the girls comes up and sits down on my right, chatting me up. She’s gorgeous, and I’m pumped.

After a few minutes, my buddy starts rubbing my leg. I’m a little confused, but figured he was giving me a “hint”, and start mirroring his behavior by rubbing the girl’s leg. After a few more minutes, he starts rubbing more vigorously. I’m thinking to myself, “this actually works?”, but nevertheless start rubbing her leg more vigorously.

The conversation quickly deteriorates, and she runs off in a hurry to join her friends on the dance floor. I turn to my buddy and he says, “take the f-ing 20!”, “What 20?”, “The $20 I’m rubbing on your leg so you can buy her a drink!”

She came back 5 minutes later wearing a wedding ring. I’m positive she wasn’t married, just applying some douche repellent.

12. Pure Fire

In high school, when I was 14 or 15, I rode the bus with a girl who had blossomed early. She was from a different group from me and we did some occasional flirting but chances for actual interaction were rare.

While we were standing around waiting for the busses to arrive one day, I noticed that she was wearing jeans shorts cut very short on top of her very long legs. For some reason, I thought it would be hilarious to light the fringe of her jeans shorts on fire with my lighter (keep in mind…I was guided only by hormones). I thought it would be like a sockfire or something. Like “woosh!” and then out.

So when her back was turned I lit the lighter right under her butt, and of course immediately the frayed cotton of the shorts went right up and showed no indication of going right out. Immediately I recognized that I had made a major error and I commenced slapping at her upper thigh/ass area in an attempt to get it out.

It did go out, but of course I had run up behind her and apparently begun roughly grabbing at her ass, from her perspective. Attempting to smooth it over with “I was trying to put out the fire that I had set upon you” didn’t go over any better, and needless to say I could have gone to jail.

She just decided to avoid me (and rightly so) from then on out.

TL;DR – I set a girl I liked on fire.

11. You Too?!

After encouragement, a drunk friend of mine wandered over to a hot chick at a loud party and stumbled into the following exchange:

“Hey! My name’s Luis! What’s your name?”

“Luis??” struggling to hear

“Haha! Oh wow! Your name’s Luis too! That’s so crazy!”


“…I’m really drunk.” wanders off

10. Not That Innocent

I was pretty innocent at 16 and was flirting with a guy on my swim team.

For some reason he was wagging his finger in my face, so I snatched it and moved it towards my face…I dunno, I think I was pretending to bite it, just being feisty.

He had this intense look on his face, and as I moved the finger to my mouth I suddenly realized, horrified, what it actually looked like.

I dropped his hand and ran out of the room- we didn’t talk for months, I was so embarrassed I didn’t even want to see him.